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2025
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Season
Winner
CONCACAF Caribbean Cup 2025
CONCACAF Caribbean Cup 2024
Cavalier
CONCACAF Caribbean Cup 2023
Robinhood
Caribbean Club Championship 2022
Violette
Caribbean Club Championship 2021
Cavaly
Caribbean Club Championship 2020
No winner
Caribbean Club Championship 2019
Robinhood
Caribbean Club Championship 2018
Atletico Pantoja
Caribbean Club Championship 2017
Cibao
CFU Club Championship 2016
Central FC
CFU Club Championship 2015
Central FC
